[(7aR)-7a-methyl-1-oxo-2,3,5,6,7,7a-hexahydro-1H-inden-5-one]propylenic thioacetal | 395641-70-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: [(7aR)-7a-methyl-1-oxo-2,3,5,6,7,7a-hexahydro-1H-inden-5-one]propylenic thioacetal
• 英文别名: (7'aR)-7'a-methylspiro[1,3-dithiane-2,5'-2,3,6,7-tetrahydroindene]-1'-one
• CAS: 395641-70-0
• 化学式: C₁₃H₁₈OS₂
• 分子量: 254.417
• InChiKey: CQJFYVMOUMBNDO-GFCCVEGCSA-N

物化性质

• 沸点：
  415.3±45.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(7aR)-7a-methyl-1-oxo-2,3,5,6,7,7a-hexahydro-1H-inden-5-one]propylenic thioacetal 在 9-borabicyclo[3.3.1]nonane dimer 、 三氟化硼乙醚 、 水 、 sodium tert-pentoxide 、 pyridinium chlorochromate 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 5.92h， 生成 (1R,7aS)-7a-methyl-5-oxo-2,3,5,6,7,7a-hexahydro-1H-indene-1-carbaldehyde
  参考文献：
  名称：

  Inotropic Activity of Hydroindene Amidinohydrazones

  摘要：

  Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+-ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human alpha(2)beta(1) isozyme (associated with the inotropic effect) with respect to the alpha(1)beta(1) isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

  DOI：

  10.1021/jm0109309
• 作为产物：
  描述：

  2-甲基-1,3-环戊二酮 在 三甲基氯硅烷 、 对甲苯磺酸 、 溶剂黄146 、 D-脯氨酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 30.0h， 生成 [(7aR)-7a-methyl-1-oxo-2,3,5,6,7,7a-hexahydro-1H-inden-5-one]propylenic thioacetal
  参考文献：
  名称：

  Inotropic Activity of Hydroindene Amidinohydrazones

  摘要：

  Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+-ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human alpha(2)beta(1) isozyme (associated with the inotropic effect) with respect to the alpha(1)beta(1) isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

  DOI：

  10.1021/jm0109309

文献信息

• Inotropic Activity of Hydroindene Amidinohydrazones
  作者：Luis G. Sevillano、Concepción P. Melero、Esther Caballero、Fernando Tomé、Lionel G. Lelièvre、Käthi Geering、Gilles Crambert、Rosalía Carrón、Manuel Medarde、Arturo San Feliciano

  DOI：10.1021/jm0109309

  日期：2002.1.1

  Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+-ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human alpha(2)beta(1) isozyme (associated with the inotropic effect) with respect to the alpha(1)beta(1) isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).